Work

Nitrate Reduction for Deaminative Suzuki–Miyaura Coupling of Anilines

Year: 2025

Type: article

Abstract: We present a deaminative Suzuki–Miyaura‐type coupling (SMC) of anilines with nitrate as a diazotization reagent, which integrates transition‐metal catalysis with nitrate‐based diazonium chemistry for the first time. The synergistic reduction of nitrate by bisulfite and boronic acids allows for both oxidative diazotization with low‐valent transition metal redox transformations simultaneously. The reaction utilizes low‐hazard, readily available starting materials and reagents. In comparison to previous diazonium‐based Suzuki–Miyaura‐couplings, the in situ oxidation of anilines by reduction of nitrate allows larger functional group tolerance.

Source: Angewandte Chemie

DOI: 10.1002/ange.202504012

Authors: Chen‐Chen Li, Áron Adorján, Manolis Sofiadis, Tim Schulte, Javier Mateos, Mike Rippegarten, Tobias Ritter

Institutions: Max-Planck-Institut für Kohlenforschung, RWTH Aachen University

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,790

OpenAlex ID: W4410035712

FWCI:

Cites: 69

Cited by:

Related to: 10